Audio file plays in my itunes but restarts my ipod

Question

I downloaded some audio files that play perfectly in my itunes but when I click on the middle button of my ipod to choose song to play, it restarts my ipod. All other files I have play in both my itunes and ipod perfectly. Thanks for help!

Answer 1

You don't have to check Manually manage music and videos, but if you want to add songs and video to the iPhone by dragging them to the iPhone in iTunes, that checkbox needs to be checked.  Otherwise, you can use the Music tab (next to the Summary tab) to set up automatic syncing, based on playlists, artists, albums, and/or genres, which for me is the more convenient way to load an iPod or iPhone.  I usually do it using playlists (that have only the songs I want on my Pod).
I don't know what's going on with that one Amazon download.  I've downloaded songs from Amazon before, and have not encountered any problems.  I haven't done so recently, so maybe I'll find something free (they have a lot of free downloads compared to the iTunes Store) and give it a try, to see if I have the same problem.
As a workaround, you can try converting the song file.  First, open iTunes preferences and click on the General tab.  Then, click Import Settings.  Make sure it is set to AAC Encoder and iTunes Plus (which should be the default settings).  This setting will encode (if you "rip" any music CDs), or convert song files, to the format used by iTunes Store downloads, which is 256 kbps ACC.
Select the Amazon download with the problem your iTunes music library listing.  Go up to the menu bar.  Under Advanced, select Create AAC Version.  (You can also select that command by right-clicking on song.)
This will convert the song file to AAC format.  The original MP3 file will still be there, but you will also have an AAC version.  You should be able to sync an AAC song file created by iTunes to your iPhone.
NOTE:  When you do this, you are converting one compressed audio format to another compressed audio format, so there may be a small loss in sound quality.  The difference is probably not noticeable when listening on an iPod or iPhone using "earbuds."  When listening to the song on the computer, you should use the original song file.